CARBENOXOLONE

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Synonyms
Status
Molecule Category UNKNOWN
ATC A02BX01
UNII MM6384NG73
EPA CompTox DTXSID4022733

Structure

InChI Key OBZHEBDUNPOCJG-WBXJDKIVSA-N
Smiles CC1(C)[C@@H](OC(=O)CCC(=O)O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12
InChI
InChI=1S/C34H50O7/c1-29(2)23-10-13-34(7)27(32(23,5)12-11-24(29)41-26(38)9-8-25(36)37)22(35)18-20-21-19-31(4,28(39)40)15-14-30(21,3)16-17-33(20,34)6/h18,21,23-24,27H,8-17,19H2,1-7H3,(H,36,37)(H,39,40)/t21-,23-,24-,27+,30+,31-,32-,33+,34+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C34H50O7
Molecular Weight 570.77
AlogP 6.83
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 117.97
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 41.0

Bioactivity

Mechanism of Action Action Reference
11-beta-hydroxysteroid dehydrogenase inhibitor INHIBITOR PubMed PubMed PubMed Other PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
82 83-1630 - 62 12-88
Enzyme
82 83-1630 - 62 12-88
Assay Description Organism Bioactivity Reference
In vitro inhibitory activity against human 11 beta hydroxysteroid dehydrogenase type 1 using scintillation proximity assay (SPA) None 330.0 nM
In vitro inhibitory activity against mouse 11 beta hydroxysteroid dehydrogenase type 1 using scintillation proximity assay (SPA). None 108.0 nM
Ability to convert [3H]cortisol to the tritium labeled cortisone in the presence of human 11 beta hydroxysteroid dehydrogenase type 2 None 83.0 nM
Inhibition of mouse microsomal 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [3H]cortisone to [3H]cortisol by scintillation proximity assay Mus musculus 82.0 nM
Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [1,2-3H]cortisone to cortisol at 1 uM after 10 mins by scintillation counting Homo sapiens 87.7 %
Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as oxidation of [1,2,6,7-3H]cortisol to cortisone at 1 uM after 10 mins by scintillation counting Homo sapiens 98.2 %
Inhibition of 11beta-HSD1 in human microsomes by HTRF cortisol assay Homo sapiens 500.0 nM
Inhibition of human 11beta-HSD1 expressed in CHO cells after 3 hrs by HTRF cortisol assay Homo sapiens 500.0 nM
Inhibition of mouse 11beta-HSD1 expressed in CHO cells after 3 hrs by HTRF cortisol assay Mus musculus 250.0 nM
Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as residual conversion of [1,2-[3H]cortisone to cortisol at 1000 nM after 10 mins by scintillation counting Homo sapiens 12.0 %
Inhibition of human 11beta-HSD2 expressed in HEK293 cells assessed as residual conversion of [1,2,6,7-[3H]cortisol to cortisone at 1000 nM after 10 mins by scintillation counting Homo sapiens 2.0 %
Inhibition of human recombinant 11beta-HSD1 expressed in HEK293 cells assessed as conversion of [1,2-[3H]cortisone to cortisol at 1 uM after 10 mins by scintillation counting Homo sapiens 87.7 %
Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [1,2-[3H]cortisone to cortisol at 1 uM after 10 mins by scintillation counting Homo sapiens 98.2 %
Inhibition of mouse 11beta-HSD2 expressed in HEK293 cells assessed as [3H]cortisol production after 60 mins by SPA Mus musculus 82.0 nM
Inhibition of mouse 11beta-HSD2 expressed in HEK293 cells assessed as conversion of [3H]cortisone into [3H]cortisol by scintillation proximity assay Mus musculus 206.0 nM
Inhibition of human 11beta-HSD1 expressed in CHO-K1 cells using cortisone as substrate after 3 hrs by HTRF assay Homo sapiens 500.0 nM
Inhibition of full-length human 11beta-HSD1 expressed in HEK293 cells at 10 uM after 2 hrs by scintillation proximity assay relative to control Homo sapiens 78.32 %
Inhibition of N-terminal MKHQHQHQHQHQHQQPL-tagged 11beta-HSD1 C272S mutant (unknown origin) expressed in Escherichia coli BL21 (DE3) using cortisol as substrate measured for 1 hr in presence of NADPH by fluorescence assay Homo sapiens 410.0 nM Inhibition of N-terminal MKHQHQHQHQHQHQQPL-tagged 11beta-HSD1 C272S mutant (unknown origin) expressed in Escherichia coli BL21 (DE3) using cortisol as substrate measured for 1 hr in presence of NADPH by fluorescence assay Homo sapiens 62.0 nM
Inhibition of 11beta-HSD2 (unknown origin) expressed in HEK293 cells using cortisone as substrate measured after 2 hrs in presence of NAD+ by HTRF assay Homo sapiens 170.0 nM
Inhibition of transglutaminase in human keratinocytes in presence of 10 uM retinal relative to retinal alone Homo sapiens 361.0 nM
Inhibition of retinal reductase in Sprague-Dawley rat liver microsomes at 100 uM using all-trans retinaldehyde and NADPH by HPLC analysis relative to control Rattus norvegicus 26.0 %
Inhibition of mouse 11beta-HSD1 expressed in CHOK1 cells using XL665-labeled cortisol as substrate measured after 24 hrs by HTRF assay Mus musculus 243.0 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL499915
DrugBank DB02329
DrugCentral 493
FDA SRS MM6384NG73
Guide to Pharmacology 4151
PDB CBO
PubChem 636403
SureChEMBL SCHEMBL76013
ZINC ZINC000003977823
CONTENTS